


Betwixt

by frumpkinisfae



Series: CR2 Kinktober 2020 [8]
Category: Critical Role (Web Series)
Genre: Cunnilingus, Dom Essek Thelyss, Dom/sub, Dry Humping, Face-Sitting, Kinktober 2020, M/M, Oral Sex, Overstimulation, POV Caleb Widogast, Sub Caleb Widogast, Subspace, Trans Caleb Widogast, Trans Essek Thelyss, Tribadism
Language: English
Status: Completed
Published: 2020-10-12
Updated: 2020-10-12
Packaged: 2021-03-07 21:34:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,231
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26960728
Author URL: https://archiveofourown.org/users/frumpkinisfae/pseuds/frumpkinisfae
Summary: “Is something the matter?” Caleb inquires quietly leaning his head on Essek’s shoulder.Essek places the paper down and removes his spectacles rubbing the bridge of his nose, “Yes and no. I am currently stuck in a fair amount of bureaucratic idiocy that I need a break from.”Caleb bites his bottom lip as he turns himself so he’s facing Essek’s right side, “I could, uh- help you relax?”Essek’s smile never fails to send butterflies through Caleb’s stomach, “You would, precious boy? How do you imagine you would accomplish that?”
Relationships: Essek Thelyss/Caleb Widogast
Series: CR2 Kinktober 2020 [8]
Series URL: https://archiveofourown.org/series/1961788
Comments: 3
Kudos: 75





	Betwixt

**Author's Note:**

> Sweet syrupy porn abound! Please enjoy!
> 
> This is my Kinktober fill for Tribbing with Essek and Caleb!
> 
> Please note, in this work, Caleb's bottom growth is referred to as "cock/dick" and his front hole is referred to as "cunt."  
> Essek's bottom growth is referred to as "cock/clit" and his front hole is referred to as "cunt/pussy." If any of that would upset you, please take care of yourself!
> 
> Enjoy the show ;)

These peaceful evenings at home are what Caleb has grown to enjoy the most. Propped up by Essek’s somewhat excessive amount of pillows and draped with one of the softest sheets he’s ever felt, Caleb thumbs through a romance novel Jester lent him. He is side by side with Essek, who is reading all manner of papers in Undercommon and penning out first drafts of responses. The air is serene, disturbed only by the quiet breaths of the pair, scratches of Essek’s quill against the papers, and pages turning.

At the conclusion of a somewhat rambling chapter, Caleb slips his bookmark in as he closes the book. He then gently leans into Essek’s side. The drow’s left arm hugs him closer as he continues to write.

Only half a year ago, Caleb would never have felt so free to show his affections like this. Essek has always been patient and kind, easing Caleb out of his shell. Anytime he tries to thank him, Essek responds saying that he feels that he never would have been as happy or felt as worthy without him. This must be what romance novels mean about completing each other.

He gazes at Essek. The drow is incredibly focused. Wearing his small golden spectacles at the end of his nose, he reads and rereads ever paper. His brow is furrowed in concentration.

“Is something the matter?” Caleb inquires quietly leaning his head on Essek’s shoulder.

Essek places the paper down and removes his spectacles rubbing the bridge of his nose, “Yes and no. I am currently stuck in a fair amount of bureaucratic idiocy that I need a break from.”

Caleb bites his bottom lip as he turns himself so he’s facing Essek’s right side, “I could, uh- help you relax?”

Essek’s smile never fails to send butterflies through Caleb’s stomach, “You would, precious boy? How do you imagine you would accomplish that?”

As Essek discards his ornate writing desk, Caleb slings his leg over Essek perched in his lap. He intends to lean in for a kiss but stops, staring into Essek’s handsome face. His pale blue eyes fanned with long white eyelashes peer back up at Caleb. A sultry smile twists his thick lips when the human raises his hands to hold either side of his dusky violet skin.

They meet each other for a long, sweet kiss. Essek’s hand grips the back of Caleb’s neck, and he melts at the possessive gesture. While Caleb may currently be on top, Essek lets him know who owns who. Kiss after kiss, the two hardly separate but for quick pants. They are totally enclosed in their own lovely erotic world.

Caleb barely notices when he begins dragging his clothed sex back and forth over Essek’s thick thigh. Essek calls attention to the movement placing a hand on Caleb’s ass gripping it tightly. He moans into the kiss at the rough treatment spurring his dominant into pulling Caleb’s briefs down and slapping the soft skin with each of Caleb’s weak thrusts, reddening the soft cheeks. 

It feels magnificent. His plumped cunt dragging tantalizingly over and over Essek’s thigh, blocked from true pleasure by pesky fabric. His cock drags through his own wetness trapped by his briefs. Every spank from Essek shocks a moan out of him.

Without warning, Caleb’s shirt is wrenched over his head and he’s pushed firmly onto his back. He’s confused and disoriented, but deep inside knows he’s safe. If anything he enjoys the slight twinge of fear.

He doesn’t notice Essek is naked until his pussy is right above his face. Essek’s cunt is gorgeous. His beautiful dark lips are spread slightly revealing his exposed purpled clit. His inner lips are thin and barely there while his outer lips are much longer, starting puffed but draw smaller. The bright sheen of arousal coat’s the entirety of Essek’s sex.

Many an evening has Caleb spent buried in his dominant’s pussy. Licking up Essek’s sweet tangy juices, enjoying the pleasured moans he receives, and melting into every piece of praise Essek gives him.

It looks like tonight may be one of those nights.

Essek lowers his pussy onto Caleb’s mouth and he immediately begins licking as best he can. Using broad strokes across the throbbing purple clit and thrusting his tongue into the hole. Caleb’s heart flutters as Essek rewards him with moans and gentle thrusts.

He repeatedly swirls his tongue around the throbbing clit. Smooth and hard, it pulses against him reassuring Caleb that he’s pleasing his dominant. Then he returns to pushing up into Essek’s pulsing hole, hot and sweet. He begins to feel as if he’s drowning in slick.

“Yes, such a good boy,” Essek’s voice is like syrup, sweet and warm in Caleb’s ears. “Working so hard for me. Mmh- Keep going. We are going to try something new in a bit. Ah- I know you will enjoy it.”

He nods. Anything Essek wants, Caleb wants.

After a few more minutes of Caleb sucking up Essek’s arousal, he whimpers as the drow suddenly pulls away. A soothing voice echos through the room and all Caleb can make out is the loving tone.

He can’t recall when, but he’s already fallen into subspace. Everything is tingly and slow. His mind feels empty but warm, wanting only to please and pleasure.

His briefs are pulled down slowly and his cunt pulses in the cool air. Essek’s hand rubs against it gently and Caleb writhes at the attention and all he can speak are whimpers.

Essek lifts up his bony hips and adjusts him so that one of his legs is cushioned on top of Essek’s thick right thigh and the other is pressed bellow the left.

Then Essek pulls him into him and Caleb sees stars. Their cunts are pressed together. He feels the warmth of Essek’s gorgeous cunt against his own as they are brought together by their sexes. The pressure and slickness are delightful. He hears Essek moan as if the human is underwater and knows he must be responding in kind, yet he has no control over his voice anymore.

The first thrust is entirely unexpected. The sensitive skin of his cunt rubbing against Essek’s who is rolling his hot mound down against Caleb’s. Bothe eagerly buck themselves into the other, chasing the orgasmic feeling.

Soon Caleb is too weak with pleasure to move and Essek grabs his waist moaning at the pressure and slick heat. He presses Caleb’s cunt into his pussy again and again and again, until by chance their pulsing cocks meet.

It’s impossible to know who orgasmed first from that touch, even if Caleb likes to believe it was simultaneous. The delicious pressure combined with the rubbing of cock on cock was too much to bear. Both men release, a high pitched scream mingling with a deep moan, with their pulsing cunts against each other. Essek rides it out with a few more thrusts and Caleb trembles in overstimulation.

Caleb feels Essek remove himself and whimpers, weakly reaching out. Quickly his waist is encircled and he’s pulled up gently into Essek’s lap.

The drow gifts him with a gentle kiss, “What a precious boy! Did you enjoy that?”

Caleb nods and his head drifts down onto Essek’s shoulder, worn out. He feels deft fingers draw soothing circles across his back as he dozes, safe, warm, and happy.

**Author's Note:**

> And then they took a nice lavender-scented bath and went to sleep. The end!
> 
> If you guys have any requests for prompts and pairings, please don't hesitate to leave them below! Next up is Teratophilia with Fjord and a Werewolf and Marking with Beauyasha!
> 
> Thank you for reading! I'd love any comments or kudos y'all have :)


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